Heck Reaction of 2-Oxyacrylates with Aryl Bromides: A Common Route to Monoaryl Pyruvates and Ortho Ester-Protected Monoaryl Pyruvates

Kiran Matcha*, Konstantin Chernichenko*, Kévin Jouvin, Suresh Babu Guduguntla, Duc N. Tran, Stephen Bell, Warren Paden, Marek Figlus, Colin Muir, Alain Elliott and Cristina Hernandez Diaz

*Chemical Process Research and Development, Janssen Pharmaceutica N.V., Turnhoutseweg 30, Beerse 2340, Belgium, Email: kmatchaits.jnj.com, kcherni1its.jnj.com

K. Matcha, K. Chernichenko, K. Jouvin, S. B. Guduguntla, D. N. Tran, S. Bell, W. Paden, M. Figlus, C. Muir, C. H. Diaz, J. Org. Chem., 2022, 87, 10736-10746.

DOI: 10.1021/acs.joc.2c00946

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Abstract

DavePhos as ligand efficiently promotes a palladium-catalyzed Heck reaction between 2-oxyacrylates and aryl bromides to provide 2-oxycinnamates, which serve as excellent precursors for the synthesis of monoaryl pyruvates or ortho ester-protected monoaryl pyruvates depending on the nature of the 2-oxy group.

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synthesis of monoaryl pyruvates

Davephos

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Key Words

Heck reaction, α-arylation

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ID: J42-Y2022